
Holiday rentals in Kailua
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Top-rated holiday rentals in Kailua
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Kailua holiday rentals
Other great holiday rentals in Kailua

Guest house in Kailua
4.79 out of 5 average rating, 180 reviewsAbsolutely Oceanfront-60'Waterfall Pool-Legal

Guest suite in Kailua
5 out of 5 average rating, 17 reviewsSteps to Lanikai Beach - Tree House - Since 1985!
Guest favourite

Flat in Waikiki
5 out of 5 average rating, 28 reviewsThe Ocean Luxe in Waikiki, 1 Parking
Guest favourite

Flat in Waikiki
4.96 out of 5 average rating, 51 reviews25FL-Upscale Ultra Modern-Premium 1BR W/Parking
Guest favourite

Cottage in North Shore
4.88 out of 5 average rating, 120 reviewsBest Kept Secret on Oahu! and WE ARE LICENSED!!!
Superhost

Flat in Waikiki
4.88 out of 5 average rating, 40 reviews37FL-Luxury Upscale Ocean View-Modern 1BR/Parking~

Tiny home in Kailua
5 out of 5 average rating, 3 reviewsAffordable Hawaii Camping Trip | Gear Included

Home in Kailua
4.84 out of 5 average rating, 134 reviewsSerenity Beachfront Cottage- NUC No 90/TVU-0326
Quick stats about holiday rentals in Kailua
Total rentals
360 properties
Total number of reviews
11K reviews
Family-friendly rentals
200 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
90 properties have a pool
Rentals with dedicated workspaces
170 properties have a dedicated workspace
Destinations to explore
- Waikiki Beach Holiday rentals
- Kihei Holiday rentals
- Kaanapali Holiday rentals
- Wailea-Makena Holiday rentals
- Napili-Honokowai Holiday rentals
- Ko Olina Beach Holiday rentals
- Haleiwa Holiday rentals
- Moloka‘i Holiday rentals
- Island of Hawai'i Holiday rentals
- Honolulu Holiday rentals
- Kauai Holiday rentals
- O‘ahu Holiday rentals
- Beach apartment rentals Kailua
- Villa rentals Kailua
- Pet-friendly rentals Kailua
- Rentals with pools Kailua
- Rentals with a kayak Kailua
- Rentals with a patio Kailua
- Beachfront rentals Kailua
- Family-friendly rentals Kailua
- Apartment rentals Kailua
- Family-friendly rentals Kailua
- Rentals with beach access Kailua
- Rentals with a washing machine and dryer Kailua
- Rentals with a hot tub Kailua
- Fitness-friendly rentals Kailua
- Waterfront rentals Kailua
- Rentals with an EV charger Kailua
- Flat rentals Kailua
- Private suite rentals Kailua
- Rentals with outdoor seating Kailua
- House rentals Kailua
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- Kailua Beach
- Waimea Bay Beach
- Ko Olina Resort
- Kepuhi Beach
- Mālaekahana Beach
- Lanikai Beach
- Kualoa Ranch
- Mākoa Beach
- Honolulu Zoo
- Banzai Pipeline
- Kapalaoa Beach
- Hanauma Bay
- Kaupoa Beach
- Ala Moana Beach Park
- White Plains Beach
- Pyramid Rock Beach
- Wet 'n' Wild Hawaii
- Diamond Head Beach Park
- Bishop Museum
- Kalama Beach
- Makao Beach
- Sans Souci Beach
- Mahakea Beach
- Ko Olina Golf Club
- Things to do Kailua
- Things to do Honolulu County
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- Things to do United States
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- Food and drink United States
- Wellness United States
- Nature and outdoors United States
- Art and culture United States
- Tours United States
- Sports activities United States
- Entertainment United States